Disclosed herein are phase change inks and methods for the use thereof. More specifically, disclosed herein are phase change inks containing modified pigment particles. One embodiment is directed to a phase change ink composition comprising (a) an ink carrier comprising (1) a polyalkylene wax and (2) a component selected from the group consisting of (A) amides, (B) esters, (C) ester-amides, (D) urethanes, (E) ureas, (F) urethane-ureas, and (G) mixtures thereof, and (b) pigment particles having hydrophobic functional groups covalently bonded to the surfaces thereof, said ink composition having a melting point no lower than about 40° C., said ink composition having a melting point no higher than about 160° C.
In general, phase change inks (sometimes referred to as “hot melt inks”) are in the solid phase at ambient temperature, but exist in the liquid phase at the elevated operating temperature of an ink jet printing device. At the jet operating temperature, droplets of liquid ink are ejected from the printing device and, when the ink droplets contact the surface of the recording substrate, either directly or via an intermediate heated transfer belt or drum, they quickly solidify to form a predetermined pattern of solidified ink drops. Phase change inks have also been used in other printing technologies, such as gravure printing, as disclosed in, for example, U.S. Pat. No. 5,496,879 and German Patent Publications DE 4205636AL and DE 4205713AL, the disclosures of each of which are totally incorporated herein by reference.
Phase change inks for color printing typically comprise a phase change ink carrier composition which is combined with a phase change ink compatible colorant. In a specific embodiment, a series of colored phase change inks can be formed by combining ink carrier compositions with compatible subtractive primary colorants. The subtractive primary colored phase change inks can comprise four component dyes, namely, cyan, magenta, yellow and black, although the inks are not limited to these four colors. These subtractive primary colored inks can be formed by using a single dye or a mixture of dyes. For example, magenta can be obtained by using a mixture of Solvent Red Dyes or a composite black can be obtained by mixing several dyes. U.S. Pat. Nos. 4,889,560, 4,889,761, and 5,372,852, the disclosures of each of which are totally incorporated herein by reference, teach that the subtractive primary colorants employed can comprise dyes from the classes of Color Index (C.I.) Solvent Dyes, Disperse Dyes, modified Acid and Direct Dyes, and Basic Dyes. The colorants can also include pigments, as disclosed in, for example, U.S. Pat. No. 5,221,335, the disclosure of which is totally incorporated herein by reference. U.S. Pat. No. 5,621,022, the disclosure of which is totally incorporated herein by reference, discloses the use of a specific class of polymeric dyes in phase change ink compositions.
Phase change inks have also been used for applications such as postal marking, industrial marking, and labelling.
Phase change inks are desirable for ink jet printers because they remain in a solid phase at room temperature during shipping, long term storage, and the like. In addition, the problems associated with nozzle clogging as a result of ink evaporation with liquid ink jet inks are largely eliminated, thereby improving the reliability of the ink jet printing. Further, in phase change ink jet printers wherein the ink droplets are applied directly onto the final recording substrate (for example, paper, transparency material, and the like), the droplets solidify immediately upon contact with the substrate, so that migration of ink along the printing medium is prevented and dot quality is improved.
Compositions suitable for use as phase change ink carrier compositions are known. Some representative examples of references disclosing such materials include U.S. Pat. Nos. 3,653,932, 4,390,369, 4,484,948, 4,684,956, 4,851,045, 4,889,560, 5,006,170, 5,151,120, 5,372,852, 5,496,879, European Patent Publication 0187352, European Patent Publication 0206286, German Patent Publication DE 4205636AL, German Patent Publication DE 4205713AL, and PCT Patent Application WO 94/04619, the disclosures of each of which are totally incorporated herein by reference. Suitable carrier materials can include paraffins, microcrystalline waxes, polyethylene waxes, ester waxes, fatty acids and other waxy materials, fatty amide containing materials, sulfonamide materials, resinous materials made from different natural sources (tall oil rosins and rosin esters, for example), and many synthetic resins, oligomers, polymers, and copolymers.
U.S. Pat. No. 4,889,560 (Jaeger et al.), the disclosure of which is totally incorporated herein by reference, discloses a phase change ink carrier composition combined with a compatible colorant to form a phase change ink composition. A thin film of substantially uniform thickness of that phase change ink carrier composition, and the ink produced therefrom, has a high degree of lightness and chroma. The thin films of a substantially uniform thickness of the ink composition are also rectilinearly light transmissive. The carrier composition is preferably a fatty amide-containing compound.
U.S. Pat. No. 4,889,761 (Titterington et al.), the disclosure of which is totally incorporated herein by reference, discloses a method for producing a light-transmissive phase change ink printed substrate is described which comprises providing a substrate, and then printing on at least one surface of the substrate a predetermined pattern of a light-transmissive phase change ink which initially transmits light in a non-rectilinear path. The pattern of solidified phase change ink is then reoriented to form an ink layer of substantially uniform thickness. This ink layer will, in turn, produce an image which then will transmit light in a substantially rectilinear path. In one aspect of the invention, the substrate is light transmissive, and the reoriented printed substrate exhibits a high degree of lightness and chroma, and transmits light in a substantially rectilinear path. In this way, the reoriented printed substrate can be used in a projection device to project an image containing clear, saturated colors.
U.S. Pat. No. 5,372,852 (Titterington et al.), the disclosure of which is totally incorporated herein by reference, discloses a phase change ink composition that is indirectly applied to a substrate by raising the temperature of the phase change ink composition to form a liquid phase change ink composition, applying droplets of the phase change ink composition in a liquid phase to a liquid intermediate transfer surface on a solid support in a pattern using a device such as an ink jet printhead, solidifying the phase change ink composition on the liquid intermediate transfer surface, transferring the phase change ink composition from the liquid intermediate transfer surface to the substrate, and fixing the phase change ink composition to the substrate. The phase change ink composition is malleable when the ink is transferred from the intermediate transfer surface to the substrate and is ductile after the ink has been transferred to the substrate and cooled to ambient temperature to preclude the ink from crumbling and cracking.
U.S. Pat. No. 5,621,022 (Jaeger et al.), the disclosure of which is totally incorporated herein by reference, discloses a phase change ink composition wherein the ink composition utilizes polymeric dyes in combination with a selected phase change ink carrier composition.
U.S. Pat. No. 5,782,966 (Bui et al.), the disclosure of which is totally incorporated herein by reference, discloses resins and waxes made by reacting selected nucleophiles, including alcohols and/or amines, with an isocyanate. The order of addition of the isocyanate and the different nucleophiles can tailor the distribution of di-urethane, mixed urethane/urea, and/or di-urea molecules in the final resin product. The isocyanate-derived resin and wax materials are useful as ingredients as phase change ink carrier compositions used to make phase change ink jet inks.
U.S. Pat. No. 5,902,841 (Jaeger et al.), the disclosure of which is totally incorporated herein by reference, discloses a phase change ink composition wherein the ink composition utilizes colorant in combination with a selected phase change ink carrier composition containing at least one hydroxy-functional fatty amide compound.
U.S. Pat. No. 5,994,453 (Banning et al.), the disclosure of which is totally incorporated herein by reference, discloses phase change carrier compositions made from the combination of at least one urethane resin; at least one urethane/urea resin; at least one mono-amide; and at least one polyethylene wax. The order of addition of the reactants to form the reactant product urethane resin and urethane/urea resin permits the tailoring or design engineering of desired properties.
U.S. Pat. No. 6,174,937 (Banning et al.), the disclosure of which is totally incorporated herein by reference, discloses a phase change ink comprising a material of the formula
wherein X1, X2, X3, and X4 are segments comprising atoms selected from groups V and VI of the periodic table; wherein at least one R1 and R5 comprises at least 37 carbon units; and wherein R2, R3, and R4 each comprise at least one carbon unit. The invention further encompasses a composition of matter, as well as methods of reducing coefficients of friction of phase change ink formulations.
U.S. Pat. No. 6,309,453 (Banning et al.), the disclosure of which is totally incorporated herein by reference, discloses colorless compounds having a central core and at least two arms extending from the core. The core can comprise one or more atoms. The at least two arms have the formula
In such formula, Z is a segment of one or more atoms; j is an integer from 1 to about 300 and can be different at one of the at least two arms than at another of the at least two arms; Q is an alkyl or aryl group and can vary amongst different alkyl and aryl groups within the colorless compound; and n is an integer greater than 1 and can be different at one of the at least two arms than at another of the at least two arms. In other aspects, the invention encompasses phase change inks incorporating the above-described colorless compound as toughening agent, and methods of printing with such phase change inks. The invention further includes a solid ink comprising a colorant and a colorless compound of the formula
In such formula, X is a single atom corresponding to N or O; Z1 and Z2 are substituents comprising one or more atoms, and can be the same as one another or different from one another; and j is an integer from 1 to about 50.
U.S. Pat. No. 6,380,423 (Banning et al.), the disclosure of which is totally incorporated herein by reference, discloses colorless compounds having a central core and at least two arms extending from the core. The core can comprise one or more atoms. The at least two arms have the formula
In such formula, Z is a segment of one or more atoms; j is an integer from 1 to about 300 and can be different at one of the at least two arms than at another of the at least two arms; Q is an alkyl or aryl group and can vary amongst different alkyl and aryl groups within the colorless compound; and n is an integer greater than 1 and can be different at one of the at least two arms than at another of the at least two arms. In other aspects, the invention encompasses phase change inks incorporating the above-described colorless compound as toughening agent, and methods of printing with such phase change inks. The invention further includes a solid ink comprising a colorant and a colorless compound of the formula
In such formula, X is a single atom corresponding to N or O; Z1 and Z2 are substituents comprising one or more atoms, and can be the same as one another or different from one another; and j is an integer from 1 to about 50.
U.S. Pat. No. 5,221,335 (Williams et al.), the disclosure of which is totally incorporated herein by reference, discloses a stabilized pigmented hot melt ink containing a thermoplastic vehicle, a coloring pigment, and a dispersion-stabilizing agent to inhibit settling or agglomeration of the pigment when the ink is molten, comprising 1.5 to 20 weight percent of a nitrogen-modified acrylate polymer. A preferred dispersion-stabilizing agent is the nitrogen-modified methacrylate polymer marketed by Rohm and Haas as Plexol 1525.
U.S. Pat. No. 5,800,600 (Lima-Marquez et al.), the disclosure of which is totally incorporated herein by reference, discloses a solid ink jet ink composition which is suitable for hot melt applications having a carrier having an electrical resistivity of at least 108 Ohm.cm, insoluble marking particles, and a particle charging agent dispersed in it. The marking particle may be a pigment, an insoluble dyestuff, a polymer, or mixture thereof. The particle charging agent may be a metal soap, a fatty acid, lecithin, an organic phosphorous compound, a succinimide, a sulfosuccinate, petroleum sulfonates, a soluble or partially soluble resin such as a modified rosin ester, an acrylic, a vinyl, a hydrocarbon, or a mixture thereof. The solid ink jet ink composition may further include a viscosity controller. The ink may be capable of being heated to 155° C. and have at that temperature a viscosity of between 5 to 150 centipoise.
U.S. Pat. No. 6,494,943 (Yu et al.), the disclosure of which is totally incorporated herein by reference, discloses colored pigments having one or more desired parameters and/or properties. These parameters and/or properties include: a) a particles size of from about 10 nm to about 300 nm; b) an accusizer number of less than 1010 particles/ml of dispersion at 15% solids which are greater than 0.5 micron; c) a filterability such that when in a liquid medium, 100 ml having 10% solids of the colored pigment filters through a 3 micron nylon absolute filter; d) a colored pigment purity of greater than about 80%, based on extractable material; and/or e) a stability such that the above-described properties do not change by more than 50% at 25° C. for at least one week. Colored pigments having at least one organic group and having one or more of the above-described characteristics is also described as well as a process for preparing surface-modified colored pigments. The process involves combining at least one treating agent and at least one type of colored pigment(s) in a container to form a mixture and subjecting the mixture to high shearing and introducing at least one diazotizing agent to the mixture at least for a portion of time while the high shearing is taking place, and preferably during the entire time that high shearing is taking place, such that a reaction product is formed and contains surface-modified colored pigment(s).
U.S. Pat. No. 6,472,471 (Cooke et al.), the disclosure of which is totally incorporated herein by reference, discloses various modified carbon products which can form a part of a polymeric product containing the modified carbon product and a polymer. One type of modified carbon product disclosed is a carbon product having attached at least one organic group, monomeric group, or polymeric group. Another type of modified carbon product disclosed is a carbon product having attached a group having the formula: —Ar—CO2—R or —CnH2nCO2—R where R is an organic group, monomeric group, or a polymeric group. The third type of modified carbon product contains a) a carbon product having attached at least one organic group directly attached to the carbon product, b) at least one ionic group, ionizable group, or a mixture thereof attached to the organic group, and c) at least one counter-ionic group or counter-ionizable group with at least one organic group, monomeric group, or polymeric group, or mixture thereof, where the counter-ionic or counter-ionizable group is attached to the ionic and/or ionizable group. A method of improving the dispersion of carbon products in polymers is also disclosed which involves dispersing the modified carbon products described above in a polymer to form a polymeric product.
U.S. Pat. No. 6,398,858 (Yu et al.), the disclosure of which is totally incorporated herein by reference, discloses a process for preparing surface-modified colored pigments. The process includes the steps of: preparing a reaction batch comprising a treating agent and a diazotizing agent; adding a colored pigment to the batch; and mixing the colored pigment and the batch under high shear conditions to form a reaction product comprising a surface-modified colored pigment. The treating agent has an organic group which comprises at least one diazotizable group. In a preferred embodiment the diazotizable group comprises a) at least one aromatic group or at least one C1-C20 alkyl group, and b) at least one ionic group, ionizable group, nonionic group, or a mixture thereof. The surface-modified colored pigments prepared by the process of the invention have been found useful in aqueous or solvent based compositions and particularly in ink jet ink compositions.
U.S. Pat. No. 5,922,118 (Johnson et al.), the disclosure of which is totally incorporated herein by reference, discloses a modified colored pigment which comprises colored pigment having attached at least one organic group. The organic group comprises a) at least one aromatic group or a C1-C12 alkyl group and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group. The aromatic group or the C1-C12 alkyl group of the organic group is directly attached to the pigment and the organic group is present at a treatment level of from about 0.10 to about 4.0 micromoles/m2 of the pigment used based on nitrogen surface area of the pigment. Also described are aqueous and non-aqueous inks and coatings and ink jet ink compositions containing the modified colored pigment. A method to increase the flow of an ink is also disclosed as well as a method to improve the waterfastness of a print imaged by an ink composition. Also, other ink jet ink compositions are described which comprise an aqueous or non-aqueous vehicle and a colored pigment having attached an organic group having the formula: Ar—R1 (I) or Ar′R3R2 (II) wherein Ar is an aromatic group and Ar′ is an aromatic group.
U.S. Pat. No. 5,713,988 (Belmont et al.), the disclosure of which is totally incorporated herein by reference, discloses a non-aqueous coating or ink composition having incorporated therein a modified carbon product comprising carbon having attached a substituted or unsubstituted aromatic group. Also described is a modified carbon product comprising carbon and an attached organic group having a) an aromatic group and b) at least one group of the formula SO2NR2 or SO2NR(COR) wherein R is independently hydrogen, a C1-C20 substituted or unsubstituted alkyl, a C3-C20 substituted or unsubstituted alkenyl, (C2-C4 alkyleneoxy)xR′ or a substituted or unsubstituted aryl; R′ is hydrogen, a C1-C20 substituted or unsubstituted alkyl, a C3-C20 substituted or unsubstituted alkenyl, C1-C20 substituted or unsubstituted alkanoyl or substituted or unsubstituted aroyl; and x is from 1 to 40.
U.S. Pat. No. 6,506,245 (Kinney et al.), the disclosure of which is totally incorporated herein by reference, discloses colored pigments having one or more desired parameters and/or properties. These parameters and/or properties include: a) a particles size of from about 10 nm to about 300 nm; b) an accusizer number of less than 1010 particles/ml of dispersion at 15% solids which are greater than 0.5 micron; c) a filterability such that when in a liquid medium, 100 ml having 10% solids of the colored pigment filters through a 3 micron nylon absolute filter; d) a colored pigment purity of greater than about 80%, based on extractable material; and/or e) a stability such that the above-described properties do not change by more than 50% at 25° C. for at least one week. Colored pigments having at least one organic group and having one or more of the above-described characteristics is also described as well as a process for preparing surface-modified colored pigments. The process involves combining at least one treating agent and at least one type of colored pigment(s) in a container to form a mixture and subjecting the mixture to high shearing and introducing at least one diazotizing agent to the mixture at least for a portion of time while the high shearing is taking place, and preferably during the entire time that high shearing is taking place, such that a reaction product is formed and contains surface-modified colored pigment(s).
U.S. Pat. No. 6,177,498 (Rehman), the disclosure of which is totally incorporated herein by reference, discloses a solvent system which aids in start-up, drop ejection, decap and high frequency firing above 10 kHz for inks which contain latex polymers. Two solvents work in conjunction with each other: 3-hexyne-2,5-diol and 1,2-octanediol. These two solvents in combination improve printability in latex polymer-containing ink-jet inks. Such ink-jet inks also include one or more pigments and a vehicle comprising at least one organic, water-miscible solvent and water.
U.S. Pat. No. 6,042,643 (Belmont et al.), the disclosure of which is totally incorporated herein by reference, discloses processes for preparing a carbon black product having an organic group attached to the carbon black. In one process at least one diazonium salt reacts with a carbon black in the absence of an externally applied electric current sufficient to reduce the diazonium salt. In another process at least one diazonium salt reacts with a carbon black in a protic reaction medium. Carbon black products which may be prepared according to process are described as well as uses of such carbon black products in plastic compositions, rubber compositions, paper compositions, and textile compositions.
U.S. Pat. No. 5,900,029 (Belmont et al.), the disclosure of which is totally incorporated herein by reference, discloses processes for coloring a fiber or textile by adding a carbon black product having an organic group attached to the carbon black. In one process at least one diazonium salt reacts with a carbon black in the absence of an externally applied electric current sufficient to reduce the diazonium salt. In another process at least one diazonium salt reacts with a carbon black in a protic reaction medium. Carbon black products which may be prepared according to process are described as well as uses of such carbon black products in plastic compositions, rubber compositions, paper compositions, and textile compositions.
U.S. Pat. No. 5,895,522 (Belmont et al.), the disclosure of which is totally incorporated herein by reference, discloses a modified carbon product which comprises carbon having attached at least one organic group wherein the organic group comprises a) at least one aromatic group or a C1-C12 alkyl group, and b) a group having the formula -AG-Sp-LG-Z, wherein AG is an activating group, Sp is a spacer group, LG is a leaving group, and Z is a counterion, and wherein the aromatic or the C1-C12 alkyl group is directly attached to the carbon, and wherein the organic group is present in any amount. The present invention also relates to ink and coating compositions comprising these modified carbon products.
U.S. Pat. No. 5,885,335 (Adams et al.), the disclosure of which is totally incorporated herein by reference, discloses a modified carbon product which comprises carbon having attached at least one organic group. The organic group comprises a) at least one aromatic group or a C1-C12 alkyl group and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group. The aromatic group or the C1-C12 alkyl group of the organic group is directly attached to the carbon and the organic group is present at a level of from about 0.10 to about 2.7 micromoles/m2 of the carbon used based on CTAB or t-area of the carbon or in an amount such that the modified carbon product has a residue value of more than about 5 weight percent. Also described are aqueous and non-aqueous inks and coatings containing the modified carbon product. A method to increase the flow of an ink, as measured by glass plate flow, by incorporating the modified carbon product as part of the ink is also disclosed. Lastly, non-aqueous ink and coating formulations are described which contain an appropriate solvent and a modified carbon product comprising carbon having attached at least one organic group, wherein the organic group comprises a) at least one aromatic group or C1-C12 alkyl group, and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group, wherein the organic group is present in any amount.
U.S. Pat. No. 5,851,280 (Belmont et al.), the disclosure of which is totally incorporated herein by reference, discloses processes for preparing a carbon black product having an organic group attached to the carbon black. In one process at least one diazonium salt reacts with a carbon black in the absence of an externally applied electric current sufficient to reduce the diazonium salt. In another process at least one diazonium salt reacts with a carbon black in a protic reaction medium. Carbon black products which may be prepared according to process are described as well as uses of such carbon black products in plastic compositions, rubber compositions, paper compositions, and textile compositions.
U.S. Pat. No. 5,837,045 (Johnson et al.), the disclosure of which is totally incorporated herein by reference, discloses a surface-modified colored pigment which includes a colored pigment having no primary amines and at least one attached hydrophilic organic group, wherein said organic group comprises a) at least one aromatic group, and b) at least one ionic group or ionizable group, or a mixture of an ionic group or an ionizable group. The colored pigment may be blue, brown, cyan, green, violet, magenta, red, orange, yellow, mixtures thereof and the like. The surface-modified colored pigment, due to the hydrophilic groups on its surface, is readily dispersed in a liquid vehicle without the addition of a surfactant or other dispersing aid or additive. The surface-modified color pigment may be used in a variety of aqueous systems including, but not limited to, coatings, paints, papers, adhesives, latexes, inks, toners, textiles and fibers. In addition, an aqueous composition is disclosed including water-based liquid vehicle and the surface-modified colored pigment described above. Also disclosed is an ink composition including a water-based liquid vehicle and the surface-modified colored pigment described above. Finally, a process is disclosed for preparing the surface-modified colored pigments having no primary amines and at least one attached hydrophilic organic group, wherein said organic group comprises a) at least one aromatic group, and b) at least one ionic or ionizable group, or a mixture of an ionic group or an ionizable group.
U.S. Pat. No. 5,803,959 (Johnson et al.), the disclosure of which is totally incorporated herein by reference, discloses a modified carbon product which comprises carbon having attached at least one organic group. The organic group comprises a) at least one aromatic group or a C1-C12 alkyl group and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group. The aromatic group or the C1-C12 alkyl group of the organic group is directly attached to the carbon and the organic group is present at a level of from about 0.10 to about 4.0 micromoles/m2 of the carbon used based on nitrogen surface area of the carbon. Also described are aqueous and non-aqueous inks and coatings and ink jet ink compositions containing the modified carbon product. A method to increase the flow of an ink, as measured by glass plate flow, by incorporating the modified carbon product as part of the ink is also disclosed as well as a method to improve the waterfastness of a print imaged by an ink composition. Lastly, non-aqueous ink and coating formulations are described which contain an appropriate solvent and a modified carbon product comprising carbon having attached at least one organic group, wherein the organic group comprises a) at least one aromatic group or C1-C12 alkyl group, and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group, wherein the organic group is present in any amount.
U.S. Pat. No. 5,707,432 (Adams et al.), the disclosure of which is totally incorporated herein by reference, discloses a modified carbon product which comprises carbon having attached at least one organic group. The organic group comprises a) at least one aromatic group or a C1-C12 alkyl group and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group. The aromatic group or the C1-C12 alkyl group of the organic group is directly attached to the carbon and the organic group is present at a level of from about 0.10 to about 2.5 micromoles/m2 of the carbon used based on CTAB or t-area of the carbon or in an amount such that the modified carbon product has a residue value of more than about 5 weight percent. Also described are aqueous and non-aqueous inks and coatings containing the modified carbon product. A method to increase the flow of an ink, as measured by glass plate flow, by incorporating the modified carbon product as part of the ink is also disclosed. Lastly, non-aqueous ink and coating formulations are described which contain an appropriate solvent and a modified carbon product comprising carbon having attached at least one organic group, wherein the organic group comprises a) at least one aromatic group or C1-C12 alkyl group, and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group, wherein the organic group is present in any amount.
U.S. Pat. No. 5,698,016 (Adams et al.), the disclosure of which is totally incorporated herein by reference, discloses a composition which comprises a) an amphiphilic ion, and b) a modified carbon product comprising carbon having attached at least one organic group. The organic group has a charge opposite to the amphiphilic ion. Also disclosed are aqueous and non-aqueous ink and coating compositions incorporating this composition. Ink jet ink compositions are further described incorporating this composition.
U.S. Pat. No. 5,672,198 (Belmont), the disclosure of which is totally incorporated herein by reference, discloses aqueous ink compositions which include a modified carbon product comprising a carbon having attached at least one organic group that is substituted with an ionic or an ionizable group. A coating composition is also described and comprises water, a binder, and a modified carbon product having at least one organic group attached to carbon wherein the organic group is substituted with an ionic or an ionizable group.
U.S. Pat. No. 5,630,868 (Belmont et al.), the disclosure of which is totally incorporated herein by reference, discloses an aqueous ink jet ink composition comprising an aqueous vehicle and a modified carbon product containing carbon having attached at least one organic group. The organic group comprises a) at least one aromatic group and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group. The organic group having an aromatic group is directly attached to the carbon by the aromatic group. The organic group may comprise a) at least one C1-C12 alkyl group and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group. Ink jet recording methods applying an ink jet ink of the present invention are also described.
U.S. Pat. No. 5,571,311 (Belmont et al.), the disclosure of which is totally incorporated herein by reference, discloses an aqueous ink jet ink composition comprising an aqueous vehicle and a carbon black product having attached at least one organic group. The organic group comprises a) at least one aromatic group and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group. The organic group is directly attached to the carbon black by an aromatic group. Also disclosed is an aqueous ink jet ink composition comprising an aqueous vehicle and a carbon black product having attached at least one organic group. The organic group comprises a) at least one C1-C12 alkyl group and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group. The organic group is directly attached to the carbon black by an alkyl group. Ink jet recording methods applying an ink jet ink of the present invention are also described.
U.S. Pat. No. 5,554,739 (Belmont), the disclosure of which is totally incorporated herein by reference, discloses processes for preparing a carbon product having an organic group attached to a carbon material. The carbon material is selected from graphite powder, a graphite fiber, a carbon fiber, a carbon cloth, a vitreous carbon product, and an activated carbon product. In one process at least one diazonium salt reacts with a carbon material in the absence of an externally applied electric current sufficient to reduce the diazonium salt. In another process at least one diazonium salt reacts with a carbon material in a protic reaction medium.
U.S. Pat. No. 5,281,261 (Lin), the disclosure of which is totally incorporated herein by reference, discloses an ink composition comprising an aqueous liquid vehicle and pigment particles having attached to the surfaces thereof a polymerized vinyl aromatic salt. In one embodiment, the polymeric vinyl aromatic salt is chemically grafted to the surfaces of the pigment particles; in another embodiment, the polymeric vinyl aromatic salt is adsorbed onto the surfaces of the pigment particles. Preferably, the modified pigment particles have an average particle diameter of less than about 1 micron. The ink composition is suitable for applications such as ink jet printing processes, particularly thermal ink jet printing processes. Images generated with ink compositions of the present invention are sharp, waterfast, lightfast, and of high optical density, exhibiting no feathering, and can be electrically conductive.
U.S. Pat. No. 5,184,148 (Suga et al.), the disclosure of which is totally incorporated herein by reference, discloses an ink comprising an aqueous liquid medium which contains acid carbon black having a volatile content within the range of 3.5 to 8 percent by weight and a water-soluble resin having a weight average molecular weight within the range of 3,000 to 30,000, wherein the weight ratio of the acid carbon black to the water-soluble resin is within the range of 3:1 to 10:1. Also disclosed are an ink jet recording method, an ink jet device, an ink cartridge, and an ink jet recording apparatus which uses the ink.
U.S. Pat. No. 4,530,961 (Nguyen et al.), the disclosure of which is totally incorporated herein by reference, discloses aqueous dispersion of carbon black grafted with hydrophilic monomers such as alkali or ammonium carboxylate bearing polymers. The dispersion has a viscosity of about 2 to about 30 cP for a carbon black content of about 1 to 15 percent by weight.
EP 0 797 635 B1 (Belmont et al.), the disclosure of which is totally incorporated herein by reference, discloses a non-aqueous coating or ink composition having incorporated therein a modified carbon product comprising carbon having attached a substituted or unsubstituted aromatic group. Also described is a modified carbon product comprising carbon and an attached organic group having a) an aromatic group and b) at least one group of the formula SO2NR2 or SO2NR(COR) wherein R is independently hydrogen, a C1-C20 substituted or unsubstituted alkyl, a C3-C20 substituted or unsubstituted alkenyl, (C2-C4 alkyleneoxy)xR′ or a substituted or unsubstituted aryl; R′ is hydrogen, a C1-C20 substituted or unsubstituted alkyl, a C3-C20 substituted or unsubstituted alkenyl, C1-C20 substituted or unsubstituted alkanoyl or substituted or unsubstituted aroyl: and x is from 1 to 40.
EP 0 797 636 B1 (Belmont et al.), the disclosure of which is totally incorporated herein by reference, discloses an aqueous ink jet ink composition comprising an aqueous vehicle and a modified carbon product containing carbon having attached at least one organic group. The organic group comprises a) at least one aromatic group and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group. The organic group having an aromatic group is directly attached to the carbon by the aromatic group. The organic group may comprise a) at least one C1-C12 alkyl group and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group. Ink jet recording methods applying an ink jet ink of the invention are also described.
EP 1 220 879 B1 (Belmont), the disclosure of which is totally incorporated herein by reference, discloses various modified pigment products which are preferably capable of being dispersed in a variety of materials such as coatings, inks, toners, films, plastics, polymers, elastomers, and the like. The modified pigments are pigments having attached a) at least one steric group and b) at least one organic ionic group and at least one amphiphilic counterion, wherein the amphiphilic counterion has a charge opposite to that of the organic ionic group. In addition, inks, coatings, toners, films, plastics, polymers, elastomers, and the like containing the modified pigment products of the invention are described. Methods of making the modified pigment products are also described.
EP 1 007 595 B1 (Belmont et al.), the disclosure of which is totally incorporated herein by reference, discloses a modified carbon product which comprises carbon having attached at least one organic group wherein the organic group comprises a) at least one aromatic group or a C1-C12 alkyl group, and b) a group having the formula -AG-Sp-LG-Z, wherein AG is an activating group, Sp is a spacer group, LG is a leaving group, and Z is a counterion, and wherein the aromatic or the C1-C12 alkyl group is directly attached to the carbon, and wherein the organic group is present in any amount. The invention also relates to ink and coating compositions comprising these modified carbon products.
EP 0 910 611 B1 (Adams et al.), the disclosure of which is totally incorporated herein by reference, discloses a modified carbon product which comprises carbon having attached at least one organic group. The organic group comprises a) at least one aromatic group or a C1-C12 alkyl group and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group. The aromatic group or the C1-C12 alkyl group of the organic group is directly attached to the carbon and the organic group is present at a level of from about 0.10 to about 2.5 micromoles/m2 of the carbon used based on CTAB or t-area of the carbon or in an amount such that the modified carbon product has a residue value of more than about 5 wt %. Also described are aqueous and non-aqueous inks and coatings containing the modified carbon product. A method to increase the flow of an ink, as measured by glass plate flow, by incorporating the modified carbon product as part of the ink is also disclosed. Lastly, non-aqueous ink and coating formulations are described which contain an appropriate solvent and a modified carbon product comprising carbon having attached at least one organic group, wherein the organic group comprises a) at least one aromatic group or C1-C12 alkyl group, and b) at least one ionic group, at least one ionizable group, or a mixture of an ionic group and an ionizable group, wherein the organic group is present in any amount.
PCT Patent Publication WO 96/18688 (Belmont et al.), the disclosure of which is totally incorporated herein by reference, discloses processes for preparing a carbon black product having an organic group attached to the carbon black. In one process at least one diazonium salt reacts with a carbon black in the absence of an externally applied electric current sufficient to reduce the diazonium salt. In another process at least one diazonium salt reacts with a carbon black in a protic reaction medium. Carbon black products which may be prepared according to the process are described as well as uses of such carbon black products in plastic compositions, rubber compositions, paper compositions, and textile compositions.
PCT Patent Publication WO 92/13983 (Pinson et al.), the disclosure of which is totally incorporated herein by reference, discloses a process for modifying the surface of carbon-containing materials by electrochemical reduction of diazonium salts, applicable in particular to carbon fibres for composite materials, and carbon-containing materials so modified. According to the process, the carbon-containing material is used as a cathode in an electrolysis unit containing a diazonium salt solution ArN2x− in an aprotic solvent and by electrochemical reduction to a suitable potential, the aromatic group (Ar) is bound to the carbon-containing material. Any aromatic group can be bound in this way to the carbon-containing material, for instance C6H4NO2, C6H4NH2, C6H4COOH, and then reacted with suitable compounds.
PCT Patent Publication WO 91/15425 (Medalia et al.), the disclosure of which is totally incorporated herein by reference, discloses carbon blacks treated with a treating agent comprising at least one compound containing at least one long chain alkenyl or alkyl group and at least one amine group. Optionally, the compound contains at least one chemical group for linking the long chain alkenyl or alkyl group with the amine group. Also disclosed are ink compositions incorporating the treated carbon blacks and processes for preparing the compositions.
PCT Patent Publication WO 96/18690 (Belmont), the disclosure of which is totally incorporated herein by reference, discloses processes for preparing a carbon product having an organic group attached to a carbon material. The carbon material is selected from graphite powder, a graphite fiber, a carbon fiber, a carbon cloth, a vitreous carbon product, and an activated carbon product. In one process at least one diazonium salt reacts with a carbon material in the absence of an externally applied electric current sufficient to reduce the diazonium salt. In another process at least one diazonium salt reacts with a carbon material in a protic reaction medium.
U.S. Pat. No. 6,110,264 (Banning et al.), the disclosure of which is totally incorporated herein by reference, discloses a phase change ink carrier composition comprising at least one anhydride/alcohol inclusive reaction product.
U.S. Pat. No. 6,048,925 (Titterington et al.), the disclosure of which is totally incorporated herein by reference, discloses urethane resins made by reacting selected nucleophiles, including alcohols, with an isocyanate. The order of addition of the isocyanate and the different nucleophiles can tailor the distribution of mixed urethane molecules in the final resin product. The final resin product can be colored or uncolored and include a toughening agent. The isocyanate-derived resin materials are useful as ingredients as phase change ink carrier compositions used to make phase change ink jet inks.
U.S. Pat. No. 5,019,166 (Schwarz), the disclosure of which is totally incorporated herein by reference, discloses a thermal ink jet printing composition comprising a dye, a liquid medium, and a surfactant selected from the group consisting of polyoxyalkylated ethers, anionic bitail fluorothio alkyls, alkyl aryl sulfonates, alkyl amine quaternary salts, and mixtures thereof. Also disclosed is a process for generating images which comprises causing the ink compositions disclosed herein to be ejected from a thermal ink jet printer in imagewise fashion onto a substrate.
U.S. Pat. No. 5,626,654 (Breton et al.), the disclosure of which is totally incorporated herein by reference, discloses an ink composition which comprises an aqueous liquid vehicle, a dye, and a vesicle-forming lipid, wherein vesicles of the lipid are present in the ink.
U.S. Pat. No. 5,633,109 (Jennings et al.), the disclosure of which is totally incorporated herein by reference, discloses an ink composition which comprises an aqueous liquid vehicle, a photochromic material, and a vesicle-forming lipid, wherein vesicles of the lipid are present in the ink.
U.S. Pat. No. 5,053,079 (Haxell et al.), the disclosure of which is totally incorporated herein by reference, discloses a dispersed, pigmented hot melt ink containing a thermoplastic vehicle, a colored pigment, and a dispersing agent to inhibit settling or agglomeration of pigment when the ink is molten comprising an isocyanate-modified microcrystalline wax or lignite wax in an amount of 2 to 100 weight percent of the weight of the vehicle. Preferred is the isocyanate-modified microcrystalline wax marketed as Petrolite WB17.
H. Kunieda et al., “Formation of Reversed Vesicles,” J. Am. Chem. Soc., 1991, 113, 1051-1052, the disclosure of which is totally incorporated herein by reference, discloses reversed or inverted vesicles in solutions of the nonionic surfactant tetraethylene glycol dodecyl ether in dodecane containing a small amount of water.
While known compositions and processes are suitable for their intended purposes, a need remains for improved phase change inks. In addition, a need remains for phase change inks having pigment colorants. Further, a need remains for phase change inks having pigment colorants wherein the pigment particles are stable and uniformly dispersed within the ink formulation. Additionally, a need remains for phase change inks having improved lightfastness. A need also remains for phase change inks that generate images of desirably high optical density. In addition, a need remains for phase change inks with the aforementioned advantages which can be prepared by energy-efficient processes. Further, a need remains for phase change inks with the aforementioned advantages which can be prepared without the need for high shear mixing. Additionally, a need remains for phase change inks that can generate high optical density images without the need for excessively high concentrations of colorant.